SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP

ABSTRACT A series of 2,2′-(5-hydroxydihydropyrimidine-1,3(2H,4H)-diyl)bis-(methylene)-disubstitutedphenols was synthesized by using a Mannich-type reaction between 1,3-diaminopropan-2-ol, paraformaldehyde and substituted phenols. These previously unreported compounds were separated from th...

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Autores principales:	Rivera,Augusto, Miranda-Carvajal,Ingrid, Ríos-Motta,Jaime
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2018
Materias:	hexahydropyrimidine Mannich bases hydrogen bonding conformational preference
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000203954
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spelling	oai:scielo:S0717-970720180002039542018-07-19SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUPRivera,AugustoMiranda-Carvajal,IngridRíos-Motta,Jaime hexahydropyrimidine Mannich bases hydrogen bonding conformational preference ABSTRACT A series of 2,2′-(5-hydroxydihydropyrimidine-1,3(2H,4H)-diyl)bis-(methylene)-disubstitutedphenols was synthesized by using a Mannich-type reaction between 1,3-diaminopropan-2-ol, paraformaldehyde and substituted phenols. These previously unreported compounds were separated from the reaction mixture by column chromatography (CC) in highly pure form with a 29%-91% yield. The effect of intramolecular hydrogen bonding on the conformation of 5-hydroxyhexahydropyrimidines has been studied. Our results show that the presence of hydroxyl groups can strongly influence the stereoelectronic relationships in the six-membered heterocyclic ring.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.63 n.2 20182018-06-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000203954en10.4067/s0717-97072018000203954
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	hexahydropyrimidine Mannich bases hydrogen bonding conformational preference
spellingShingle	hexahydropyrimidine Mannich bases hydrogen bonding conformational preference Rivera,Augusto Miranda-Carvajal,Ingrid Ríos-Motta,Jaime SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
description	ABSTRACT A series of 2,2′-(5-hydroxydihydropyrimidine-1,3(2H,4H)-diyl)bis-(methylene)-disubstitutedphenols was synthesized by using a Mannich-type reaction between 1,3-diaminopropan-2-ol, paraformaldehyde and substituted phenols. These previously unreported compounds were separated from the reaction mixture by column chromatography (CC) in highly pure form with a 29%-91% yield. The effect of intramolecular hydrogen bonding on the conformation of 5-hydroxyhexahydropyrimidines has been studied. Our results show that the presence of hydroxyl groups can strongly influence the stereoelectronic relationships in the six-membered heterocyclic ring.
author	Rivera,Augusto Miranda-Carvajal,Ingrid Ríos-Motta,Jaime
author_facet	Rivera,Augusto Miranda-Carvajal,Ingrid Ríos-Motta,Jaime
author_sort	Rivera,Augusto
title	SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
title_short	SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
title_full	SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
title_fullStr	SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
title_full_unstemmed	SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
title_sort	synthesis of 5-hydroxydihydropyrimidine derivatives and the influence of intramolecular hydrogen bonding on their nmr properties and conformational preferences of the hydroxyl group
publisher	Sociedad Chilena de Química
publishDate	2018
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000203954
work_keys_str_mv	AT riveraaugusto synthesisof5hydroxydihydropyrimidinederivativesandtheinfluenceofintramolecularhydrogenbondingontheirnmrpropertiesandconformationalpreferencesofthehydroxylgroup AT mirandacarvajalingrid synthesisof5hydroxydihydropyrimidinederivativesandtheinfluenceofintramolecularhydrogenbondingontheirnmrpropertiesandconformationalpreferencesofthehydroxylgroup AT riosmottajaime synthesisof5hydroxydihydropyrimidinederivativesandtheinfluenceofintramolecularhydrogenbondingontheirnmrpropertiesandconformationalpreferencesofthehydroxylgroup
_version_	1714200925082484736

SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP

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